Dichloromethane → 2-Phenyl-5-(2-phenylpyrimidin-5-yl)oxazole

HRID 42304Notes

Reaction equation

HRID 42304 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl.Br[C:24]1[CH:25]=[N:26][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[N:28][CH:29]=1.[C:36]1([C:42]2[O:43][CH:44]=[CH:45][N:46]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(=O)([O-])[O-].[Ag+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[C:36]1([C:42]2[O:43][C:44]([C:24]3[CH:25]=[N:26][C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[N:28][CH:29]=3)=[CH:45][N:46]=2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 5892802-Phenyl-1,3-oxazoleHCID 143877455-Bromo-2-phenylpyrimidine

Product 1

HCID 592523852-Phenyl-5-(2-phenylpyrimidin-5-yl)oxazoleYield 11%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 178418647HCID 178418647, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Silver carbonate (317 mg, 1.15 mmol), triphenylphosphine (16 mg, 0.06 mmol) and Pd(dppf)Cl2.CH2Cl2 (24 mg, 5 mole %) were stirred together at room temperature under nitrogen. 5-Bromo-2-phenylpyrimidine (163 mg, 0.69 mmol) was added followed by 2-phenyl-oxazole (84 mg, 0.58 mmol; prepared according to Ohnmacht, S. A. et al., Chemical Communications, 2008, 1241-1243). Finally water (6 mL) was added and the mixture heated for 18 hours at 60° C. The mixture was cooled to room temperature and filtered through Celite washing with DCM and acetone. Purification by silica gel flash chromatography (100% DCM) through a 12-g Silicycle® flash silica cartridge gave title compound as light yellow solid (19 mg, 11% yield); Rf 0.68 with DCM; melting point 228-231° C.; 1H-NMR (300 MHz; DMSO-d6) δ 9.39 (s, 2H), 8.45 (dd, 2H), 8.17 (dd, 2H), 8.11 (s, 1H), 7.54-7.65 (m, 6H); MS (ESI+) m/z 300 (M+1), (ESI−) m/z 298 (M−1); H-PGDS FPBA IC50: 125 μM.

Workup

  1. customprepared
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through Celite
  4. washwashing with DCM and acetone
  5. customPurification by silica gel flash chromatography (100% DCM) through a 12-g Silicycle® flash silica cartridge

Sources & evidence

ORD record
ord-dd6b0107a0a94b75b6b5a9128fef319d
Source dataset
uspto-grants-2013_09
Patent number
US08536185B2

Reaction notes

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